diff --git a/openhands/agenthub/codeact_agent/codeact_agent.py b/openhands/agenthub/codeact_agent/codeact_agent.py
index ecb756781abe..974839e568cf 100644
--- a/openhands/agenthub/codeact_agent/codeact_agent.py
+++ b/openhands/agenthub/codeact_agent/codeact_agent.py
@@ -433,26 +433,6 @@ def _get_messages(self, state: State) -> list[Message]:
                 ],
             )
         ]
-        example_message = self.prompt_manager.get_example_user_message()
-        if example_message:
-            messages.append(
-                Message(
-                    role='user',
-                    content=[TextContent(text=example_message)],
-                    cache_prompt=self.llm.is_caching_prompt_active(),
-                )
-            )
-
-        # Repository and runtime info
-        additional_info = self.prompt_manager.get_additional_info()
-        if self.config.enable_prompt_extensions and additional_info:
-            # only add these if prompt extension is enabled
-            messages.append(
-                Message(
-                    role='user',
-                    content=[TextContent(text=additional_info)],
-                )
-            )
 
         pending_tool_call_action_messages: dict[str, Message] = {}
         tool_call_id_to_message: dict[str, Message] = {}
@@ -460,6 +440,7 @@ def _get_messages(self, state: State) -> list[Message]:
         # Condense the events from the state.
         events = self.condenser.condensed_history(state)
 
+        is_first_message_handled = False
         for event in events:
             # create a regular message from an event
             if isinstance(event, Action):
@@ -501,11 +482,20 @@ def _get_messages(self, state: State) -> list[Message]:
             for response_id in _response_ids_to_remove:
                 pending_tool_call_action_messages.pop(response_id)
 
-            for message in messages_to_add:
-                if message:
-                    if message.role == 'user':
-                        self.prompt_manager.enhance_message(message)
-                    messages.append(message)
+            for msg in messages_to_add:
+                if msg:
+                    if msg.role == 'user' and not is_first_message_handled:
+                        is_first_message_handled = True
+                        # compose the first user message with examples or repo/runtime info
+                        self.prompt_manager.enhance_first_user_message(
+                            msg, self.config.enable_prompt_extensions
+                        )
+
+                    # enhance the user message with additional context based on keywords matched
+                    if msg.role == 'user':
+                        self.prompt_manager.enhance_message(msg)
+
+                    messages.append(msg)
 
         if self.llm.is_caching_prompt_active():
             # NOTE: this is only needed for anthropic
@@ -513,7 +503,7 @@ def _get_messages(self, state: State) -> list[Message]:
             # https://github.com/anthropics/anthropic-quickstarts/blob/8f734fd08c425c6ec91ddd613af04ff87d70c5a0/computer-use-demo/computer_use_demo/loop.py#L241-L262
             breakpoints_remaining = 3  # remaining 1 for system/tool
             for message in reversed(messages):
-                if message.role == 'user' or message.role == 'tool':
+                if message.role in ('user', 'tool'):
                     if breakpoints_remaining > 0:
                         message.content[
                             -1
diff --git a/openhands/utils/prompt.py b/openhands/utils/prompt.py
index 1ffd4b8f117b..d1c1f2ddd343 100644
--- a/openhands/utils/prompt.py
+++ b/openhands/utils/prompt.py
@@ -205,6 +205,30 @@ def enhance_message(self, message: Message) -> None:
                 micro_text += '\n</extra_info>'
                 message.content.append(TextContent(text=micro_text))
 
+    def enhance_first_user_message(
+        self,
+        message: Message,
+        enable_prompt_extensions: bool,
+    ) -> None:
+        """
+        Add example_message and additional_info into the first user message.
+        """
+        # Get additional info, if enabled
+        additional_info = None
+        if enable_prompt_extensions:
+            additional_info = self.get_additional_info() or None
+
+        # And insert the new content at the start of the list
+        if additional_info:
+            message.content.insert(0, TextContent(text=additional_info))
+
+        # Fetch the sample user text, if any
+        example_message = self.get_example_user_message() or None
+
+        # And insert it at the start
+        if example_message:
+            message.content.insert(0, TextContent(text=example_message))
+
     def add_turns_left_reminder(self, messages: list[Message], state: State) -> None:
         latest_user_message = next(
             islice(